Wax ester compositions and methods of manufacture

ABSTRACT

Implementations of wax ester compositions may include: a product of transesterifying oleyl oleate, stearyl stearate, and behenyl behenate using one of a chemical or an enzyme catalyst. The ratio of the oleyl oleate to stearyl stearate to behenyl behenate in the mixture prior to transesterification is one of 65%/23%/12%, 56%/29%/15%, or 36%/34%/30%, respectively, measured by weight. The product may demonstrate a substantially equivalent physical property to a physical property of a transesterified wax ester composition including a jojoba ester.

BACKGROUND 1. Technical Field

Aspects of this document relate generally to compositions for syntheticwax ester compositions. More specific implementations involve syntheticcompositions to be used in cosmetic products.

2. Background

Conventionally, to obtain jojoba esters with the physical and chemicalproperties observed, oil must be extracted from the collected seeds ofthe jojoba plant. The oil is then processed through atransesterification process.

SUMMARY

Implementations of wax ester compositions may include: a product oftransesterfying three esters derived from fatty acids and fatty alcoholsusing one of a chemical catalyst, an enzyme catalyst, a bio-basedcatalyst or any combination thereof. The ratio of the three esters inthe mixture prior to transesterification is one of 65%/23%/12%,56%/29%/15%, or 36%/34%/30%, of a first ester, a second ester, and athird ester respectively, measured by weight of the mixture. The productmay demonstrate a substantially equivalent physical property to aphysical property of a transesterified wax ester composition including ajojoba ester.

Implementations of wax ester compositions may include one, all, or anyof the following:

The product may demonstrate an equivalent sensory attribute to thetransesterified wax ester composition comprising the jojoba ester.

The product may demonstrate an equivalent functional attribute to thetransesterified wax ester composition comprising the jojoba ester.

The three esters are derived from fatty acids including oleic acid,stearic acid, and behenic acid, and from fatty alcohols comprising oleylalcohol, stearyl alcohol, and behenyl alcohol, respectively.

The physical property may be one of iodine value and dropping point.

The average molecular weight of the product may be less than an averagemolecular weight of the transesterified wax ester composition includingthe jojoba ester.

The sensory attribute may be one of feel, texture, or playtime.

The functional attribute may be viscosity, color, or stability.

The three esters have carbon chain lengths between 18 to 22 carbons.

The carbon chain length distribution may range between 34 to 44 carbonsin length with a peak at 36 carbons.

The transesterified wax ester composition including the jojoba ester mayhave a carbon chain length distribution range between 36 to 46 carbonswith a peak at 42 carbons.

Implementations of wax ester compositions may include: a syntheticproduct of three or more esters derived from fatty acids and fattyalcohols using one of a chemical catalyst, an enzyme catalyst, abio-based catalyst, or any combination thereof. The synthetic productmay demonstrate a substantially equivalent physical property to aphysical property of a transesterified wax ester composition including abotanically derived jojoba ester.

Implementations of wax ester compositions may include one, all, or anyof the following:

The synthetic product may comprise a carbon chain length distributionrange between 34 to 44 carbons in length with a peak at 36 carbons andthe transesterified wax ester composition including the jojoba ester mayhave a carbon chain length distribution range between 36 to 46 carbonswith a peak at 42 carbons.

The synthetic product may demonstrate an equivalent sensory attribute tothe transesterified wax ester composition including the jojoba ester.

The synthetic product may demonstrate an equivalent functional attributeto the transesterified wax ester composition including the jojoba ester.

The physical property may be one of iodine value or dropping point.

The average molecular weight of the synthetic product is less than anaverage molecular weight of the transesterified wax ester compositionincluding the jojoba ester.

The sensory attribute may be one of feel, texture, or playtime.

The functional attribute may be viscosity, color, or stability.

The peak carbon chain length of the synthetic product may be 36 carbons.

Implementations of a wax ester composition may include a product oftransesterifying a first ester and a second ester where the first esterand the second ester are each derived from fatty acids and fattyalcohols using a chemical catalyst, an enzyme catalyst, a bio-basedcatalyst, or any combination thereof. The ratio of the first ester tothe second ester in the mixture prior to transesterification may be33.3% to 66.7% measured by weight of the mixture. The product maydemonstrate a substantially equivalent physical property to a physicalproperty of a transesterified wax ester composition comprising a jojobaester.

The foregoing and other aspects, features, and advantages will beapparent to those artisans of ordinary skill in the art from theDESCRIPTION and DRAWINGS, and from the CLAIMS.

BRIEF DESCRIPTION OF THE DRAWINGS

Implementations will hereinafter be described in conjunction with theappended drawings, where like designations denote like elements, and:

FIG. 1 is a graph comparing the Iodine Value and Dropping Point ofimplementations of a synthetic wax ester composition and botanicallyderived jojoba esters;

FIG. 2 is a graph comparing the Average Molecular Weight and Droppingpoint of implementations of a synthetic wax ester composition andbotanically derived jojoba esters;

FIG. 3 is a graph comparing the Wax Ester Distribution ofimplementations of synthetic wax ester compositions and botanicallyderived jojoba esters each having an iodine value of 66;

FIG. 4 is a graph comparing the Wax Ester Distribution ofimplementations of synthetic wax ester compositions and botanicallyderived jojoba esters each having an iodine value of 60; and

FIG. 5 is a graph comparing the Wax Ester Distribution ofimplementations of synthetic wax ester compositions and botanicallyderived jojoba esters each having an iodine value of 44.

DESCRIPTION

This disclosure, its aspects and implementations, are not limited to thespecific components, assembly procedures or method elements disclosedherein. Many additional components, assembly procedures and/or methodelements known in the art consistent with the intended wax estercompositions will become apparent for use with particularimplementations from this disclosure. Accordingly, for example, althoughparticular implementations are disclosed, such implementations andimplementing components may comprise any shape, size, style, type,model, version, measurement, concentration, material, quantity, methodelement, step, and/or the like as is known in the art for such wax estercompositions and implementing components and methods, consistent withthe intended operation and methods.

Implementations of wax ester compositions as described herein replicatethe sensory and functional attributes of jojoba based productscategorized as jojoba esters by the International Nomenclature ofCosmetics Ingredients (INCI). The implementations of wax estersdisclosed herein are synthetic as they are not naturally observed. Invarious implementations, the attributes of synthetic wax estercompositions may include feel, texture, playtime, dropping point, iodinevalue, viscosity, color and stability. Implementations of wax estercompositions may replicate the sensory and functional attributes ofjojoba ester products marketed under the tradenames of FLORAESTERS 20,FLORAESTERS 30 and FLORAESTERS 60 by International Flora Technologies,Ltd. of Chandler, Ariz.

Implementations of wax ester compositions disclosed herein may besynthesized using a combination of two or more esters in specific ratiosthat display various attributes originally only seen in jojoba esterswhich come from the seed of the jojoba plant. The starting materials forimplementations of wax ester compositions as described herein includeoleyl oleate, stearyl stearate, and behenyl behenate. In otherimplementations, a wax ester composition may include two or more estersderived from fatty acids and fatty alcohols. In various implementationsthe fatty acids may include oleic acid, stearic acid, and behenic acid,and the fatty alcohols may include oleyl alcohol, stearyl alcohol, andbehenyl alcohol. The two or more esters may include carbon chain lengthsbetween 18 to 22 carbons. In other implementations, the two or moreesters may include carbon chain length distribution ranges between 34 to44 carbons. In some implementations, individual fatty alcohols and fattyacids may be used in lieu of esterified wax ester starting materials.Examples of additional suitable individual fatty alcohols and fattyacids from various sources that may be used in various implementationsinclude, by non-limiting example, triglycerides, caprylic,octyldodecanol, ethylhexyl palmitate, dicaprylyl carbonate, sunfloweroil (high oleic acid content), coconut oil, palm kernel oil, cocoabutter, avocado oil, palm oil, olive oil, almond oil, neem oil, canolaoil, borage oil, sesame oil, wheat germ, corn oil, soybean oil,sunflower oil (low oleic content), kukui, chia seed oil, grape seed oil,rice bran oil, hemp oil, safflower oil, and other ester-containing oilsuseful as ingredients for cosmetics.

Oleyl oleate is an ester of oleyl alcohol and oleic acid. Oleyl oleatehas a chemical formula of C₃₆H₆₈O₂, a molecular weight of 532.94 g/mol,and a melting point of 14-16 degrees Celsius. Oleyl oleate may bederived from, by non-limiting example, various animal fats, vegetablefats, oils including olive oil, wheat germ oil, coconut oil, flaxseedoil, almond oil, safflower oil, and the like or any combination thereof.It may also be obtained commercially from inedible tallow which may berendered from the fat of beef or mutton. It may also be possible toobtain oleyl oleate from purely synthetic sources through chemicalreaction from various precursors. Oleyl oleate is a liquid and may beused in foods, soft soaps, bar soaps, permanent wave hair solutions,creams, nail polish, lipsticks, hair conditioning agents, skinsconditions agents and as an emollient. Oleyl oleate may also be listedas (Z)-octadec-9-enyl oleate; 9-octadecenoic acid (9Z);(9Z)-9-octadecenyl ester; 9-octadecenoic acid, 9-octadecenyl ester;9-octadecenyl ester 9-octadecenoic acid; 9octadecenoic acid (Z);9-octadecenyl ester, (Z); oleic acid, oleyl ester; or oleyl ester oleicacid. Derivatives of oleyl oleate may include oleyl stearate and oleylpalmitate.

Stearyl stearate is an ester of stearyl alcohol and stearic acid.Stearyl stearate has a chemical formula of C₃₆H₇₂O₂ and a molecularweight of 536.97 g/mol. Stearyl stearate may be prepared from, bynon-limiting example, whale oil, animal fats, vegetable oil, plantsources, cocoa butter and shea butter. It may also be possible to obtainstearyl stearate from purely synthetic sources through chemical reactionfrom various precursors. Stearyl stearate is a mixture of solid alcoholsand may be used in medicines, creams, rinses, shampoos, and othersimilar products. Stearyl stearate may also be listed as, bynon-limiting example, octadecanoic acid, octadecyl ester; octadecanoicacid, octadecyl ester, stearic acid, stearyl ester, octadecyl esteroctadecanoic acid, and octadecyl stearate. Derivatives of stearylstearate may include stearamine oxide, stearyl acetate, stearylcaprylate, stearyl citrate, stearyldimethyl amine, stearylglycyrrhetinate, stearyl heptanoate, stearyl octanoate, and stearylstearate.

Behenyl behenate is an ester of behenyl alcohol and behenic acid.Behenyl behenate has a chemical formula of C₄₄E₁₈₈O₂ and a molecularweight of 649.19 g/mol. Behenyl behenate may be derived from, bynon-limiting example, seeds of the Ben-oil tree (Moringa oleifera), oilsand oil bearing plants including pracaxi oil, rapeseed oil, canola oil,peanut oils and peanut skins. It may also be possible to obtain behenylbehenate from purely synthetic sources through chemical reaction fromvarious precursors. Behenyl behenate is a dry powder and may be used inhair conditioners, moisturizers, lubricating oils, anti-foaming agents,floor polishes and candles. Behenyl behenate may also be listed asdocosyl docosanoate; docosanyl docosanoate; docosanoic acid, docosylester, docosyl behenate, Pelemol BB, and Kester Wax BB.

Implementations of wax ester compositions like those disclosed hereinare manufactured by combining oleyl oleate, stearyl stearate, andbehenyl behenate in specific ratios by measured weight. In a particularimplementation, the ratios are 56% oleyl oleate, 23% stearyl stearate,and 12% behenyl behenate. In another implementation, the ratio is 56%oleyl oleate, 29% stearyl stearate, and 15% behenyl behenate. In anotherimplementation, the ratio is 36% oleyl oleate, 34% stearyl stearate, and30% behenyl behenate. These various implementations are listed in Table1 below. Once combined in any of the previously mentioned ratios in thisdocument, the composition is then transesterfied through a chemicalprocess, bio-based catalyst process, enzyme catalyst process, anycombination thereof, or any other known processes in the art. Anexplanation of transesterifying through the use of a catalytic processmay be found in U.S. patent application Ser. No. 14/841,242 by Jeff Addyet al, titled “Processes and Systems for Catalytic Manufacture of WaxEster Derivatives,” filed Aug. 31, 2015, and published as U.S. PatentPublication 20160177350, the disclosure of which is incorporatedentirely herein by reference.

Without being bound by any theory, it is believed that the synthesis ofwax ester compositions through the transesterification of thesematerials in appropriate ratios achieves the completely unexpectedresult of demonstrating a substantially equivalent physical property toa transesterified wax ester composition derived from jojoba esters. Forexample, the synthesized wax ester compositions disclosed hereindemonstrate an equivalent sensory attribute to a transesterified waxester composition including jojoba ester. The sensory attributes of theproduct may include a substantially equivalent feel, texture, orplaytime to the transesterified wax ester composition including jojobaester. The synthesized wax ester product demonstrates an equivalentfunctional attribute to the transesterified wax ester compositionincluding the jojoba ester. By non-limiting example, the functionalattributes of the product may include viscosity, color, or stability.Implementations of wax ester compositions as described herein may beutilized as cost effective substitutions having the attributesassociated with jojoba ester products including the FLORAESTERS 20,FLORAESTERS 30 and FLORAESTERS 60.

TABLE 1 Oleyl Stearyl Behenyl Behenate Material Oleate C36:2 StearateC36:0 C44:0 SYNOBA20  65%   23%   12% SYNOBA30  56%   29%   15% SYNOBA60 36%   34%   30% SYNOBA70 0.0% 33.3% 66.7%

The implementations of wax esters products were surprisingly shown toreplicate the physical properties of the jojoba esters as well. In oneexample, the physical properties included the dropping points of theproduct. The synthesized wax ester products were shown to replicate thedropping point of the jojoba esters while having similar iodine valuesand despite having lower molecular weights as illustrated in Table 2.The unsaturation within the molecules would specifically be expected tobe in the cis configuration. One skilled in the art would expect a waxester based lipid with equal degrees of unsaturation and iodine valuesto have similar dropping points. One skilled in the art would alsoexpect a higher molecular weight species to have a higher dropping pointcompared to a lower molecular weight compound with a similar iodinevalue. The implementations of wax ester compositions, labeled SYNOBA inthe tables, did not exhibit these expected characteristics instead theSYNOBA compounds have lower average molecular weights than the naturallyderived jojoba esters while having the same dropping point. This is acompletely unexpected result.

TABLE 2 Iodine Avg. Molecular Dropping Material Value Wt. (g/mol) Point(° C.) SYNOBA 20 65 540.6 44 SYNOBA 30 61 544.1 50 SYNOBA 60 42 552.9 58FLORAESTERS 20 66 612.2 44 FLORAESTERS 30 60 612.7 50 FLORAESTERS 60 44613.7 58

Referring now to FIG. 1, the graph illustrates that the SYNOBAcompositions have similar iodine values and dropping points whencompared to the FLORAESTERS compounds. Referring to FIG. 2, the graphillustrates that the SYNOBA compounds have the same dropping point asthe FLORAESTERS compounds while having substantially lower molecularweights. The figures indicate that the dropping point has a higherdependency on the iodine value when compared to the average molecularweight of the compositions. Without being bound by any theory, it isbelieved that the slopes generated in FIG. 1 and FIG. 2 are nearly thesame due to the polymorphism characteristics of partially saturated waxester compositions. Polymorphism is the ability of solid materialsincluding crystals to exist in more than one form or crystal structure.Double bonds in the cis configuration inhibit crystallization byinterrupting the stacking mechanism of crystal formation due to thelarger intermolecular forces and bulkier molecular structure typicallypresent in cis configurations. The only source of unsaturation in thecompositions disclosed in this document is from the oleyl alcohol andoleic acid. Those skilled in the art would understand that jojoba oilhas much more variation in unsaturated fatty alcohols and fatty acids.Both unsaturated fatty alcohols and fatty acids are evenly distributedamong all the present wax esters during the transesterification reactionfor both products. The more consistent unsaturated wax esters of thecompositions disclosed in this document are believed to lead to moreefficient packing of the molecules and therefore a more stable polymorphwhen compared to jojoba-derived equivalents. The tightly packed waxester polymorphs of the compositions disclosed in this document have ahigher heat of crystallization leading to the unexpected observation ofa higher dropping point despite having a lower average molecular weightbut equal degree of unsaturation.

Referring to FIGS. 3, 4 and 5, the distribution of the individual waxester species of compositions disclosed in this document and theFLORAESTERS compositions referred to previously is illustrated.Referring to FIG. 3, the composition illustrated (SYNOBA 20) has aniodine value of 66. Referring to FIG. 4, the composition illustrated(SYNOBA 30) has an iodine value of 60. Referring to FIG. 5, thecomposition (SYNOBA 60) illustrated has an iodine value of 44. Thesecharts illustrate that the synthesized wax ester products disclosedherein have a smaller carbon chain length distribution compared to thejojoba esters. The wax ester products are shown to have a peak carbonchain length of 36 carbons while the carbon chain length distributionranges between 34 to 44 carbons in length. The carbon chain lengths ofthe wax ester products are smaller on average than the jojoba estercompounds which have a carbon chain length distribution range between 36to 46 carbons with a peak at 42 carbons.

Additionally, the implementations of wax esters had similarfunctionality when used in a cosmetics formulation. Referring to Table3, a composition like that disclosed herein (SYNOBA 20) and thatmarketed as FLORAESTERS 20 were put into the formulations shown. Theformulated SYNOBA 20 and FLORAESTERS 20 lotions had a similar feel,viscosity, texture, color and stability. An additional formulation testwas conducted with the same formula to compare SYNOBA 30 and FLORAESTERS30. Again, the aesthetics and stability were similar, further showingthat the compositions disclosed herein are suitable substitutes forthose marketed under the FLORAESTERS tradename and other jojoba esterproducts and compositions despite having a different wax ester profileand average molecular weight. Therefore, the compositions like thosedisclosed herein may be suitable for use in cosmetics such as lotions,facial cleansers, moisturizers, makeup removers, lip conditions, shavinggels, or similar applications as a substitute for jojoba oil and jojobaester containing compositions.

TABLE 3 SYNOBA FLORAESTERS 20 20 Phase Trade Name INCI Supplier %wt./wt. % wt./wt. A Deionized Water Water — 66.27 66.27 Versene ® Na2Crystals Disodium EDTA The Dow Chemical 0.03 0.03 Co. B Glycerin, USPGlycerin The Dow Chemical 5.00 5.00 Co. Keltrol ® CG-T Xantham Gum CPKelco 0.30 0.30 C Floramac Macadamia Oil Macadamia Intefrifolia SeedFloratech 3.00 3.00 Oil FLORAESTERS 20 or SYNOBA Floratech 3.00 20 Radia7779 Ethyhexyl Palmitate Oleon 3.00 3.00 Biochemica Cocoa ButterTheobroma Cacao (Cocoa) Hallstar 5.00 5.00 White Seed Butter Florasun 90Helianthus Annuus Floratech 2.00 2.00 (Sunflower) Seed Oil Botanisil ®CP-33 Cyclopentasiloxane Botanigenics, Inc. 4.00 4.00 Dow Corning ® 200Fluid Dimethicone Dow Corning 0.50 0.50 Corporation Lexemul ® 561Glyceryl Stearate (and) PEG- Inolex Chemicals 4.00 4.00 100 StearateEmulgade PL ® 68/50 Cetearyl Glucoside (and) Cognis Corporation 3.003.00 Cetearyl Alcohol D Phenonip ® Phenoxyethanol (and) Clariant 0.900.90 Methylparaben (and) Corporation Ethylparaben (and) Butylparaben(and) Propylparaben (and) Isobutylparaben Total 100 100

TABLE 4 Oleyl Oleate Stearyl Stearate Behenyl Behenate min max min maxmin max SYN20 64 70 19 24 10 14 SYN30 55 61 20 25 13 16 SYN60 35 40 3133 28 32 SYN70 0 0 30 35 65 70

Table 4 lists the ranges of weight percentages for each component of thetotal mixture pre-transesterification in which the results observed inthis document regarding the similar properties document in this documenthave been observed.

In places where the description above refers to particularimplementations of wax ester compositions and implementing components,sub-components, methods and sub-methods, it should be readily apparentthat a number of modifications may be made without departing from thespirit thereof and that these implementations, implementing components,sub-components, methods and sub-methods may be applied to other waxester compositions.

What is claimed is:
 1. A wax ester composition comprising: a product oftransesterifying three esters derived from fatty acids and fattyalcohols using one of a chemical catalyst, an enzyme catalyst, abio-based catalyst and any combination thereof where the ratio of thethree esters in the mixture prior to transesterification is one of65%/23%/12%, 56%/29%/15%, and 36%/34%/30%, of a first ester, secondester, and a third ester, respectively, measured by weight of themixture; wherein the three esters are derived from oleic acid and oleylalcohol, stearic acid and stearyl alcohol, and behenic acid and behenylalcohol.
 2. The composition of claim 1, wherein the average molecularweight of the product is less than an average molecular weight of atransesterified wax ester composition comprising a jojoba ester.
 3. Thecomposition of claim 1, wherein the carbon chain length distribution ofthe product ranges between 34 to 44 carbons in length with a peak at 36carbons.
 4. The composition of claim 2, wherein the transesterified waxester composition comprising the jojoba ester has a carbon chain lengthdistribution range between 36 to 46 carbons with a peak at 42 carbons.5. A wax ester composition comprising: a synthetic product oftransesterifying three or more esters derived from fatty acids and fattyalcohols using one of a chemical enzyme, an enzyme catalyst, a bio-basedcatalyst, and any combination thereof; wherein the three or more esterscomprise three esters derived from oleic acid and oleyl alcohol, stearicacid and stearyl alcohol, and behenic acid and behenyl alcohol.
 6. Thecomposition of claim 5, wherein the average molecular weight of thesynthetic product is less than an average molecular weight of atransesterified wax ester composition comprising a jojoba ester and thepeak carbon chain length of the synthetic product is 36 carbons.
 7. Awax ester composition comprising: a product of transesterifying a firstester and a second ester, the first ester and the second ester eachderived from fatty acids and fatty alcohols using one of a chemicalcatalyst, an enzyme catalyst, a bio-based catalyst and any combinationthereof where the ratio of the first ester to the second ester in themixture prior to transesterification is 33.3%/66.7%, measured by weightof the mixture; wherein the first ester and the second ester areselected from the group consisting of esters derived from oleic acid andoleyl alcohol, stearic acid and stearyl alcohol, and behenic acid andbehenyl alcohol.